Intermolecular Interaction of [60]Fullerene with Tröger's Base Analogues

• Published in: Fullerenes, nanotubes, and carbon nanostructures Vol. 22; no. 1-3; pp. 66 - 74
• Main Authors: Yamada, Michio, Tokutomi, Konomi, Takehara, Ayaka, Sakai, Yusuke, Maeda, Yutaka, Hasegawa, Tadashi
• Format: Journal Article
• Language: English
• Published: Philadelphia, PA Taylor & Francis 01.01.2014
• Subjects: CH; Cross-disciplinary physics: materials science; rheology; Exact sciences and technology; Fullerenes and related materials; diamonds, graphite; interaction; Materials science; molecular recognition; Physics; Specific materials; Tröger's base; π/π; Intermolecular interaction; Fluorene; C; Experimental design; Supramolecular structure; Fullerenes; Molecular recognition; Tröger's base; Mass spectroscopy; CH/π interaction; π/π interaction
• ISSN: 1536-383X; 1536-4046
• DOI: 10.1080/1536383X.2013.787608

Tröger's base (TB, 1) and its analogues were synthesized and were subject to the titration experiments to evaluate their ability of supramolecular complexation with C 60 . Results demonstrate clearly that the fluorene-based TB analogue (2) and the bioctylfluorene-based TB analogue (3) show 1:1 binding with C 60 to form the corresponding complexes while TB 1 does not. Titration experiments exhibited that the association constant (K ass ) of 3/C 60 (48.1 ± 7.9 M −1 ) was larger than that of 2/C 60 (13.7 ± 1.4 M −1 ) . The formation of the 1:1 binding complexes 2/C 60 and 3/C 60 was also confirmed by MALDI-TOF mass spectrometry. Theoretical calculations suggest that 2 and 3 have appropriate cavities to embrace C 60 . These findings indicate that not only the π/π interaction between the fluorene moieties and the C 60 surface but also the CH/π interaction between the octyl groups and the C 60 surface serve efficiently in the supramolecular complexation with C 60 .